sodium 7-formyl-4-methoxy-3H-spiro[1-benzofuran-2,1'-cyclohexane]-6-carboxylate

ID: ALA385643

PubChem CID: 44416644

Max Phase: Preclinical

Molecular Formula: C16H17NaO5

Molecular Weight: 290.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)[O-])c(C=O)c2c1CC1(CCCCC1)O2.[Na+]

Standard InChI:  InChI=1S/C16H18O5.Na/c1-20-13-7-10(15(18)19)12(9-17)14-11(13)8-16(21-14)5-3-2-4-6-16;/h7,9H,2-6,8H2,1H3,(H,18,19);/q;+1/p-1

Standard InChI Key:  DLSDICLCCKZJFP-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    0.0098   -7.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0098   -8.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209   -9.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322   -8.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322   -7.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209   -7.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5473   -5.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1310   -4.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3029   -4.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1050   -5.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1379   -6.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3068   -6.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0511   -7.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -7.0904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273   -5.5962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372   -6.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5382   -4.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621   -4.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1219   -3.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3712   -5.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7803   -4.8683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -7.9917    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 12  1  0
 11 12  2  0
 12 13  1  0
  6 13  1  0
  6 14  1  0
 14 11  1  0
  1  2  1  0
 15 16  1  0
 10 15  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
 17 18  1  0
 17 19  2  0
  8 17  1  0
  4  5  1  0
  7 20  1  0
  5  6  1  0
 11  7  1  0
 20 21  2  0
M  CHG  2  18  -1  22   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 290.31

Molecular Weight (Monoisotopic): 290.1154

AlogP: 2.84

#Rotatable Bonds: 3

Polar Surface Area: 72.83

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.88

CX Basic pKa: ┄

CX LogP: 2.79

CX LogD: -0.43

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.87

Np Likeness Score: 0.85

References

1. Useglio M, Castellano PM, Operto MA, Torres R, Kaufman TS..  (2006)  Synthesis of 3H-spiro[benzofuran-2,1'-cyclohexane] derivatives from naturally occurring filifolinol and their classical complement pathway inhibitory activity.,  16  (19): [PMID:16875818] [10.1016/j.bmcl.2006.07.029]

Source

Source(1):

• Scientific Literature